National governments and international bodies like the United Nations (UN) and the European Union impose economic sanctions to force changes in behavior, whether that is through coercion, deterrence, punishment or shame to the countries, entities and individuals that endanger their interests or violate international norms of behavior. Sanctions are also used to advance foreign policy goals like counterterrorism, nonproliferation, and the promotion of democracy and human rights. For the US, the Trump administration’s sanctions program to pressure and deprive the Maduro regime economically has been prominent in the news lately and is considered a lower-cost, lower-risk, middle course of action between diplomacy and the use of military force to restore democracy in Venezuela. This article will examine the intent of US sanctions and distinguish between the different types of sanctions while assessing their positive and negative impacts in the cases of Cuba and Venezuela. The complex and dynamic nature of these sanctions programs underscores the need for compliance officers to keep constantly abreast of changes to designations.